After viewing some recent androgynous photos, I have to admit to a double standard – I love the traditional flip on style with women wearing men’s clothing but not so much the reverse. However, I think the one of the factors in my opinion is that the men tend to skew toward shock rather than subtlety. I wonder if it’s because they have a greater need to be noticed so as to break down a barrier; I’m not sure. Still, to be honest, the social “norm” is the filter that pops up first in my brain – men still look silly to me in dresses, whereas women are poking fun at the rigidity of men’s style and taking it to another level.

I really appreciate your willingness to self-reflect about your responses here. So please allow me to toss you another idea to consider: the gentlemen in the green coat and little sandals from a few photos back is wearing an ensemble that would work beautifully on any woman from 20 to 70–it’s a very conservative, almost old-fashioned look. There’s nothing at all “shocking” about the look itself. He’s simply dressed in the coded-feminine equivalent of what the woman above is wearing–a full-on classic look traditionally associated with a particular sex. However, since, as you note, cultural paradigms about what men are “supposed” to wear are very strong and often deeply ingrained, viewers may read his ensemble as a deliberately shocking or provocative look simply because it’s a “woman’s” look worn by a man. The reaction of shock is created by the disruption of ideologically-structured interpretive strategies, not by the clothing itself or by the man; therefore, even a very subtle, conservatively-dressed man in non-gender-traditional clothing may be read as “shocking” or deliberately provocative even when, looked at from a purely sartorial standpoint, he isn’t.

I agree – it’s all about one’s perspective. You can take it one step further by ascribing one’s fashion decisions as an extension of one’s personality and passion – there are so many gradations of androgeny. For instance, perhaps the young man who wore a fishnet top wishes to be taken at first glance as a woman in an almost sexual way; the Asian man who wears a stylish dress appears to simply love women’s clothing and is all in; this pictured woman and the young woman several posts back looking at a food menu on the street choose to walk the fine line between the traditional rolls, causing one to pause and wonder: is she or is he? I prefer the latter where subtlety and subdued style creates a clean look no matter what side the aisle they happen to choose. They also happen to appear to be having fun with subtle cues rather than making sociopolitical statements. I wonder if the more drastic approaches are an effort to obliterate the traditional roles of male and gender roles as defined by clothing. Personally, I prefer the traditional roles and distinctions between the two sexes. Time will tell…

If she was unique I might like this. But since it is a general trend (this confusion of the sexes) and I don’t like it as that.

Although it’s true, as westcosttiger says, that men look sillier imitating women, than the other way around. Women’s sexuality is somehow more malleable so they can hold the look without seeming foolish.

Helmut Newton created a portfolio of women dressed as men, in the company of conventionally dressed women. He remarked that at the conclusion of the shoot everyone was exhausted, and the women dressed as men couldn’t wait to put on dresses and party.